9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether

Base Information

• Chemical Name: 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether
• CAS No.: 72519-94-9
• Molecular Formula: C₄₂H₆₄O₉S
• Molecular Weight: 745.031
• Mol file: 72519-94-9.mol

Synonyms:

Chemical Property of 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether

There total 8 articles about 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) → 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F2 methyl ester 11,15-bistetrahydropyranyl ether (72519-94-9,101758-82-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

2: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

3: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

4: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

5: K₂CO₃ / methanol / 1 h / 45 °C

6: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature

With sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl cis-4-n-propylcyclohexanecarboxylate (101691-32-1) → 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F2 methyl ester 11,15-bistetrahydropyranyl ether (72519-94-9,101758-82-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, hexane, -78 deg C, 2.5 h

2: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

3: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

4: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

5: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

6: K₂CO₃ / methanol / 1 h / 45 °C

7: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature

With n-butyllithium; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.36.1128

Reference yield:

dimethyl 2-oxo-2-cis-(4-n-propylcyclohexyl)ethyl phosphonate (101691-28-5) → 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F2 methyl ester 11,15-bistetrahydropyranyl ether (72519-94-9,101758-82-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

2: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

3: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

4: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

5: K₂CO₃ / methanol / 1 h / 45 °C

6: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature

With sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.36.1128

upstream raw materials:

zinc(II) tosylate

15-trans-(4-α-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F_2α methyl ester

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

methyl cis-4-n-propylcyclohexanecarboxylate

Downstream raw materials:

15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-6,9α-nitriloprostaglandin F₁ methyl ester

9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester